When I first stumbled upon The Great Discontent by Tina and Ryan Essmaker many years ago, I thought one thing: great fucking name.
The magazine itself turned out to be wonderful, too—I reference it to this day when talking about great editorial design, interview technique and community building. The name though left an indelible mark on me.
I don’t think I’ve ever bothered to validate the origin of the name, because I felt it deep in my gut as soon as I saw it. I knew that I was part of that class—the class of the great discontent. I knew that it had been bestowed on me, and that it was both a blessing and a curse.
A friend recently asked what piece of work I’d shipped that I was most proud of, and I found it difficult to answer. Even more difficult than I thought I might. I’ve thought about it since and why it felt complicated, and the best I’ve got is this: I’m regularly proud of the work I’m doing, but I find it much harder to be proud of the work I’ve done.
The reason for that, I think, is twofold: I value collaboration so much that the real joy of making for me is in the beautiful, messy process, and; you can feel yourself getting better whilst making things, but once you’ve actually finished it you’re better than when you started. Of course few things are ever truly finished, but I think you get the point.
I might be misremembering, but I recall Frank Chimero talking about this when he reflected on the the writing of his book, The Shape of Design. In my memory it went something like this: once you get to the end of a draft you’re better than when you started, but that’s basically true in perpetuity so you’ll never really be satisfied.
Of course with a physical book there really is something finished—you have to print it, bind it, and ship an actual artifact to someone. I mostly design software, so surely I could simply update it? We’re often talking about work done months or years ago though. Work that’s difficult or impossible to revisit. As good as bound and shipped.
I called it both a blessing a curse because I really believe that it is—the curse that makes it difficult to feel truly proud of past work is identical to the blessing that keeps me striving for more. Striving is part of my personality. Striving is the thing that I am actually proud of.
All of that to say: I don’t think that I’ll ever feel totally comfortable with the question, but I feel completely comfortable with the reasons why. The question made me reflect on when I do feel pride, and why. It made me glad that I keep striving. That I always will.